Citizen of The Year

Police Booking Photo

Police Booking Photo

Jeffrey AndersonCity Paper

To white-collar prosecutors he's a target. According to Drug Enforcement Agency documents and a deceased narcotics prosecutor, he's a violent drug trafficker. But to people he's done business with and public officials who know him, he's a plain, soft-spoken, and successful minority businessman.

Tillman's holdings are substantial. He and his son Milton Tillman III own more than 20 companies and more than $10 million in real estate in Baltimore City and surrounding areas. He also owned two nightclubs in the 1990s. He was convicted for attempted bribery in 1993 and in '96 for tax fraud. Some who have done business with him fondly refer to him as "The Emperor."

Tillman has long shown an interest in politics, with at least $8,250 in contributions since 2001 to some of the state's highest elected officials, including $1,000 in January to Maryland Comptroller Peter Franchot (whose campaign says he will return the money). Also since 2001, Tillman captured much of the city's bail-bond market from mostly white businessmen who controlled it for decades. When he was prosecuted in state court in 2007 for fraudulent use of property as bond collateral, the minority-business community cried foul. "The trial is significant in that it raises serious question as to whether there are two systems of justice and whether race is a factor in prosecutions of minority businesses who become pioneers in new industries," read an article posted on the Maryland-Washington Minority Contractors Association web site. A Baltimore City jury acquitted Tillman, his son, and others.

Yet despite two stints in federal prison and persistent government investigations, Tillman plays it close to the line. He has mutual business interests with underworld figures and others who associate with hard-core criminals, prompting widespread speculation and accusations in federal court that connect him to Baltimore's drug trade. One of his bail bonds companies is located at a property owned by a notorious fugitive of Greek descent. Law enforcers sarcastically refer to Tillman as "Citizen of the Year."

State Sen. Joan Carter Conway's husband, Vernon "Tim" Conway, an inspector with the Baltimore City Board of Liquor License Commissioners, grew up with Tillman. The Conways run a tax service on East Monument Street across from Tillman's businesses. In an interview with City Paper in May, Sen. Conway described him as "a quiet individual, low-key, no entourage." She said high-level fraud prosecutions should target bankers, investors, and lawyers who facilitate Baltimore's underground economy, implying the government should stop harassing Tillman unless it has evidence he committed a crime. "The big boys never fall," she added.

Informed of the recent raid, Conway reiterated: "The government is always investigating something. If Mr. Tillman committed a crime, so be it. He has a reputation out there. Is it true? I don't know."

The stories below examine various aspects and associates of Tillman's business universe, as the federal probe of one of the city's most enigmatic figures unfolds. Numerous attempts to reach Tillman Jr. for comment on these stories were unsuccessful. Court documents related to the investigation can be viewed here.